Reaktion #509307

Reaktionsgleichung

N,N′-dimethyl ethylenediamine

1-bromo-3-methoxy-5-methylbenzene

NaI

→

1-iodo-3-methoxy-5-methylbenzene

Ausbeute 87.0%

Lösungsmittel

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigedried
2. 2
   Sonstigesealed tube
3. 3
   Sonstigethe tube sealed with a rubber septum
4. 4
   Sonstigeflushed with a stream of nitrogen for 15 min
5. 5
   Sonstigecap
6. 6
   Temperaturthe sealed tube was heated at 110° C. in an oil bath for 18 h
7. 7
   Temperaturto cool to room temperature
8. 8
   Sonstigequenched with a saturated aqueous solution of ammonium chloride
9. 9
   ExtraktionThe reaction mixture was extracted with CH2Cl2
10. 10
    WaschenThe organic layer was washed with water
11. 11
    Einengenconcentrated to dryness

Vorschrift

Cu(I)I (0.05 g, 0.25 mmol) and NaI (1.49 g, 10 mmol) were added to an oven dried sealed tube and the tube sealed with a rubber septum and flushed with a stream of nitrogen for 15 min. Anhydrous dioxane (5 mL), N,N′-dimethyl ethylenediamine (0.055 mL, 0.50 mmol) and 1-bromo-3-methoxy-5-methylbenzene (1) (1.0 g, 5.0 mmol) were added via a syringe with vigorous stirring under a stream of nitrogen at room temperature. The rubber septum was replaced with the Teflon cap and the sealed tube was heated at 110° C. in an oil bath for 18 h. The reaction was allowed to cool to room temperature and then quenched with a saturated aqueous solution of ammonium chloride. The reaction mixture was extracted with CH2Cl2. The organic layer was washed with water, and then concentrated to dryness to give 1-iodo-3-methoxy-5-methylbenzene (2) (1.05 g, 87% yield) as a pale yellow oil.

Quelle